JP2005518330A5 - - Google Patents
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- JP2005518330A5 JP2005518330A5 JP2002582930A JP2002582930A JP2005518330A5 JP 2005518330 A5 JP2005518330 A5 JP 2005518330A5 JP 2002582930 A JP2002582930 A JP 2002582930A JP 2002582930 A JP2002582930 A JP 2002582930A JP 2005518330 A5 JP2005518330 A5 JP 2005518330A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- cycloalkyl
- dihydro
- piperidinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 184
- -1 phenyloxy Chemical group 0.000 claims 162
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 84
- 150000001875 compounds Chemical class 0.000 claims 84
- 229910052739 hydrogen Inorganic materials 0.000 claims 75
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 65
- 229910052736 halogen Inorganic materials 0.000 claims 65
- 150000002367 halogens Chemical class 0.000 claims 64
- 125000003545 alkoxy group Chemical group 0.000 claims 60
- 239000001257 hydrogen Substances 0.000 claims 59
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 57
- 125000001424 substituent group Chemical group 0.000 claims 52
- 150000002431 hydrogen Chemical class 0.000 claims 46
- 125000001072 heteroaryl group Chemical group 0.000 claims 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
- 125000003118 aryl group Chemical group 0.000 claims 39
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 32
- 125000003282 alkyl amino group Chemical group 0.000 claims 28
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 24
- 125000002619 bicyclic group Chemical group 0.000 claims 24
- 125000004043 oxo group Chemical group O=* 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 20
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000002950 monocyclic group Chemical group 0.000 claims 16
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 16
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 7
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
- 125000004442 acylamino group Chemical group 0.000 claims 4
- 125000001118 alkylidene group Chemical group 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- LILQJVUJTFIDBY-UHFFFAOYSA-N 1-[4-(cyclooctylmethylamino)cyclohexyl]-3-ethylbenzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1C(CC1)CCC1NCC1CCCCCCC1 LILQJVUJTFIDBY-UHFFFAOYSA-N 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- NYVMZCZHOYEYOU-UHFFFAOYSA-N 1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-3-ethylbenzimidazol-2-one Chemical compound C1CC2CCCCC2CC1N1C2=CC=CC=C2N(CC)C1=O NYVMZCZHOYEYOU-UHFFFAOYSA-N 0.000 claims 1
- LQMJWHNITHLMNQ-UHFFFAOYSA-N 1-(1-benzyl-3-methylpiperidin-4-yl)-3h-indol-2-one Chemical compound C1CC(N2C3=CC=CC=C3CC2=O)C(C)CN1CC1=CC=CC=C1 LQMJWHNITHLMNQ-UHFFFAOYSA-N 0.000 claims 1
- HVSVAPSADCIRKD-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C(CC1)CCN1CC1=CC=CC=C1 HVSVAPSADCIRKD-UHFFFAOYSA-N 0.000 claims 1
- KEKPRYDDAKAEDT-UHFFFAOYSA-N 1-[1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-3-methylpiperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C1C(C)CN(C2CC3CCCCC3CC2)CC1 KEKPRYDDAKAEDT-UHFFFAOYSA-N 0.000 claims 1
- IGCBPFKTRVLSHK-UHFFFAOYSA-N 1-[1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-3-methylpiperidin-4-yl]-3h-indol-2-one Chemical compound C1CC2CCCCC2CC1N1CC(C)C(N2C3=CC=CC=C3CC2=O)CC1 IGCBPFKTRVLSHK-UHFFFAOYSA-N 0.000 claims 1
- GCFAUTUJXLEZQZ-UHFFFAOYSA-N 1-[1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)piperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C1CCN(C2CC3CCCCC3CC2)CC1 GCFAUTUJXLEZQZ-UHFFFAOYSA-N 0.000 claims 1
- MGIADQYKMHMDKW-UHFFFAOYSA-N 1-[1-(1,2,3,4-tetrahydronaphthalen-2-yl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1CC2=CC=CC=C2CC1N(CC1)CCC1N1C2=CC=CC=C2CC1=O MGIADQYKMHMDKW-UHFFFAOYSA-N 0.000 claims 1
- VUUHLRJNVMRQFC-UHFFFAOYSA-N 1-[1-(2,3-dihydro-1h-inden-2-yl)piperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C1CCN(C2CC3=CC=CC=C3C2)CC1 VUUHLRJNVMRQFC-UHFFFAOYSA-N 0.000 claims 1
- LINLVGOKXHRSPY-UHFFFAOYSA-N 1-[1-(2,3-dihydro-1h-inden-2-yl)piperidin-4-yl]-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C1CCN(C2CC3=CC=CC=C3C2)CC1 LINLVGOKXHRSPY-UHFFFAOYSA-N 0.000 claims 1
- LXZJSJZYHGABNV-UHFFFAOYSA-N 1-[1-(2,3-dihydro-1h-inden-2-yl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1C2=CC=CC=C2CC1N(CC1)CCC1N1C2=CC=CC=C2CC1=O LXZJSJZYHGABNV-UHFFFAOYSA-N 0.000 claims 1
- NWRGLIDLRXTJSD-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)-3-methylpiperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C(C(C1)C)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 NWRGLIDLRXTJSD-UHFFFAOYSA-N 0.000 claims 1
- DLYVRZLQLQGFEN-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)-3-methylpiperidin-4-yl]-3h-indol-2-one Chemical compound C1CC(N2C3=CC=CC=C3CC2=O)C(C)CN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 DLYVRZLQLQGFEN-UHFFFAOYSA-N 0.000 claims 1
- UVPYEOSMQKEYFY-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)piperidin-4-yl]-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C(CC1)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 UVPYEOSMQKEYFY-UHFFFAOYSA-N 0.000 claims 1
- FYPZKVTXDSIOLG-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 FYPZKVTXDSIOLG-UHFFFAOYSA-N 0.000 claims 1
- KUPBDFJAIIJODB-UHFFFAOYSA-N 1-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C1CCN(C2C3CCC(C3)C2)CC1 KUPBDFJAIIJODB-UHFFFAOYSA-N 0.000 claims 1
- KXABEEPGAKHMPP-UHFFFAOYSA-N 1-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C1CCN(C2C3CCC(C3)C2)CC1 KXABEEPGAKHMPP-UHFFFAOYSA-N 0.000 claims 1
- XZNQOCYOECGHKR-UHFFFAOYSA-N 1-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1C1C(C2)CCC2C1 XZNQOCYOECGHKR-UHFFFAOYSA-N 0.000 claims 1
- NJRSRMBYKJLFSR-UHFFFAOYSA-N 1-[1-(5-methylhexan-2-yl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1CN(C(C)CCC(C)C)CCC1N1C2=CC=CC=C2CC1=O NJRSRMBYKJLFSR-UHFFFAOYSA-N 0.000 claims 1
- OUYGWBQPUSQZFK-UHFFFAOYSA-N 1-[1-(cyclooctylmethyl)-3-methylpiperidin-4-yl]-3h-indol-2-one Chemical compound C1CC(N2C3=CC=CC=C3CC2=O)C(C)CN1CC1CCCCCCC1 OUYGWBQPUSQZFK-UHFFFAOYSA-N 0.000 claims 1
- XLRVRCJVURLQLB-UHFFFAOYSA-N 1-[1-(cyclooctylmethyl)piperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C(CC1)CCN1CC1CCCCCCC1 XLRVRCJVURLQLB-UHFFFAOYSA-N 0.000 claims 1
- OVQQQOSKVXWEGY-UHFFFAOYSA-N 1-[1-(cyclooctylmethyl)piperidin-4-yl]-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C(CC1)CCN1CC1CCCCCCC1 OVQQQOSKVXWEGY-UHFFFAOYSA-N 0.000 claims 1
- QAWBKQCFIWTTBQ-UHFFFAOYSA-N 1-[1-(cyclooctylmethyl)piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1CC1CCCCCCC1 QAWBKQCFIWTTBQ-UHFFFAOYSA-N 0.000 claims 1
- LTWVTPVZLGXHMI-UHFFFAOYSA-N 1-[1-(naphthalen-1-ylmethyl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1=CC=C2C(CN3CCC(CC3)N3C4=CC=CC=C4CC3=O)=CC=CC2=C1 LTWVTPVZLGXHMI-UHFFFAOYSA-N 0.000 claims 1
- ZDTVVSZPPORAQV-UHFFFAOYSA-N 1-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1=CC=CC2=CC(CN3CCC(CC3)N3C4=CC=CC=C4CC3=O)=CC=C21 ZDTVVSZPPORAQV-UHFFFAOYSA-N 0.000 claims 1
- KPTFMFIHJMRPTM-UHFFFAOYSA-N 1-[1-[(4-phenylmethoxyphenyl)methyl]piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1OCC1=CC=CC=C1 KPTFMFIHJMRPTM-UHFFFAOYSA-N 0.000 claims 1
- BRBIKOPPKYMIJR-UHFFFAOYSA-N 1-[1-[(4-phenylphenyl)methyl]piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 BRBIKOPPKYMIJR-UHFFFAOYSA-N 0.000 claims 1
- DXPPDNQYXUVLDF-UHFFFAOYSA-N 1-[3-methyl-1-(4-propan-2-ylcyclohexyl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1CC(C(C)C)CCC1N1CC(C)C(N2C3=CC=CC=C3CC2=O)CC1 DXPPDNQYXUVLDF-UHFFFAOYSA-N 0.000 claims 1
- ICQXAZSNLVCTLF-UHFFFAOYSA-N 1-[3-methyl-1-(4-propylcyclohexyl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1CC(CCC)CCC1N1CC(C)C(N2C3=CC=CC=C3CC2=O)CC1 ICQXAZSNLVCTLF-UHFFFAOYSA-N 0.000 claims 1
- GJINFLWSMJVTAH-UHFFFAOYSA-N 1-[3-methyl-1-(5-methylhexan-2-yl)piperidin-4-yl]-3h-indol-2-one Chemical compound CC1CN(C(C)CCC(C)C)CCC1N1C2=CC=CC=C2CC1=O GJINFLWSMJVTAH-UHFFFAOYSA-N 0.000 claims 1
- FMCFTRWLTULAKX-UHFFFAOYSA-N 1-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-ylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound C1CC2CCCCC2CC1NC(CC1)CCC1N1C2=CC=C(C(=O)N)C=C2NC1=O FMCFTRWLTULAKX-UHFFFAOYSA-N 0.000 claims 1
- BDWZSPNHKYJSMH-UHFFFAOYSA-N 1-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-ylamino)cyclohexyl]-3-ethylbenzimidazol-2-one Chemical compound C1CC2CCCCC2CC1NC(CC1)CCC1N1C2=CC=CC=C2N(CC)C1=O BDWZSPNHKYJSMH-UHFFFAOYSA-N 0.000 claims 1
- YDOWFVONEZMYAA-UHFFFAOYSA-N 1-[4-(2,3-dihydro-1h-inden-2-ylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(CC1)CCC1N1C2=CC=C(C(=O)N)C=C2NC1=O YDOWFVONEZMYAA-UHFFFAOYSA-N 0.000 claims 1
- LUYWJVZXBWBINH-UHFFFAOYSA-N 1-[4-(5-methylhexan-2-ylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound C1CC(NC(C)CCC(C)C)CCC1N1C(=O)NC2=CC(C(N)=O)=CC=C21 LUYWJVZXBWBINH-UHFFFAOYSA-N 0.000 claims 1
- JOQMZORIMNMWNO-UHFFFAOYSA-N 1-[4-(benzylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound O=C1NC2=CC(C(=O)N)=CC=C2N1C(CC1)CCC1NCC1=CC=CC=C1 JOQMZORIMNMWNO-UHFFFAOYSA-N 0.000 claims 1
- TYSMIRKJWOUVRO-UHFFFAOYSA-N 1-[4-(benzylamino)cyclohexyl]-3-ethylbenzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1C(CC1)CCC1NCC1=CC=CC=C1 TYSMIRKJWOUVRO-UHFFFAOYSA-N 0.000 claims 1
- RDQLCLLGFNYKLN-UHFFFAOYSA-N 1-[4-(cyclooctylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound O=C1NC2=CC(C(=O)N)=CC=C2N1C(CC1)CCC1NC1CCCCCCC1 RDQLCLLGFNYKLN-UHFFFAOYSA-N 0.000 claims 1
- KWOYLCCMQIYFLV-UHFFFAOYSA-N 1-[4-(dibenzylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound O=C1NC2=CC(C(=O)N)=CC=C2N1C(CC1)CCC1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 KWOYLCCMQIYFLV-UHFFFAOYSA-N 0.000 claims 1
- OOUXBZOOFSNPDU-UHFFFAOYSA-N 1-[4-[benzyl(2,3-dihydro-1h-inden-2-yl)amino]cyclohexyl]-3-ethylbenzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1C(CC1)CCC1N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 OOUXBZOOFSNPDU-UHFFFAOYSA-N 0.000 claims 1
- SFGGSFKSBNZWNX-UHFFFAOYSA-N 1-benzyl-3-ethylbenzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1CC1=CC=CC=C1 SFGGSFKSBNZWNX-UHFFFAOYSA-N 0.000 claims 1
- LDWLKZLPOVQLOH-UHFFFAOYSA-N 1-ethyl-3-(4-propylcyclohexyl)benzimidazol-2-one Chemical compound C1CC(CCC)CCC1N1C(=O)N(CC)C2=CC=CC=C21 LDWLKZLPOVQLOH-UHFFFAOYSA-N 0.000 claims 1
- FCXWYYMEXWVASJ-UHFFFAOYSA-N 1-ethyl-3-(5-methylhexan-2-yl)benzimidazol-2-one Chemical compound C1=CC=C2N(C(C)CCC(C)C)C(=O)N(CC)C2=C1 FCXWYYMEXWVASJ-UHFFFAOYSA-N 0.000 claims 1
- NMOONDNEDCFSGW-UHFFFAOYSA-N 1-ethyl-3-(naphthalen-1-ylmethyl)benzimidazol-2-one Chemical compound C1=CC=C2C(CN3C4=CC=CC=C4N(C3=O)CC)=CC=CC2=C1 NMOONDNEDCFSGW-UHFFFAOYSA-N 0.000 claims 1
- QKFZSJPUZHFGHY-UHFFFAOYSA-N 1-ethyl-3-(naphthalen-2-ylmethyl)benzimidazol-2-one Chemical compound C1=CC=CC2=CC(CN3C4=CC=CC=C4N(C3=O)CC)=CC=C21 QKFZSJPUZHFGHY-UHFFFAOYSA-N 0.000 claims 1
- DAODRBATUZJZHS-UHFFFAOYSA-N 1-ethyl-3-[(4-phenylmethoxyphenyl)methyl]benzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1CC(C=C1)=CC=C1OCC1=CC=CC=C1 DAODRBATUZJZHS-UHFFFAOYSA-N 0.000 claims 1
- GWIYEJNNCJDCCP-UHFFFAOYSA-N 1-ethyl-3-[(4-phenylphenyl)methyl]benzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1 GWIYEJNNCJDCCP-UHFFFAOYSA-N 0.000 claims 1
- FLWIPFTXSGPABH-UHFFFAOYSA-N 1-ethyl-3-[4-(naphthalen-2-ylamino)cyclohexyl]benzimidazol-2-one Chemical compound C1=CC=CC2=CC(NC3CCC(CC3)N3C4=CC=CC=C4N(C3=O)CC)=CC=C21 FLWIPFTXSGPABH-UHFFFAOYSA-N 0.000 claims 1
- SUOCZWNUONQVBE-UHFFFAOYSA-N 1-ethyl-3-[4-[(4-phenylmethoxyphenyl)methylamino]cyclohexyl]benzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1C(CC1)CCC1NCC(C=C1)=CC=C1OCC1=CC=CC=C1 SUOCZWNUONQVBE-UHFFFAOYSA-N 0.000 claims 1
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| US28466701P | 2001-04-18 | 2001-04-18 | |
| US28466801P | 2001-04-18 | 2001-04-18 | |
| US28466901P | 2001-04-18 | 2001-04-18 | |
| US28466601P | 2001-04-18 | 2001-04-18 | |
| PCT/US2002/012351 WO2002085357A1 (en) | 2001-04-18 | 2002-04-18 | Nociceptin analogs |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009150369A Division JP5189562B2 (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
| JP2009150370A Division JP2009263380A (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
| JP2009150368A Division JP5081870B2 (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
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| EP (7) | EP1930322A1 (https=) |
| JP (4) | JP4364513B2 (https=) |
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| BR (1) | BR0209129A (https=) |
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- 2002-04-18 EP EP05014117A patent/EP1598340B1/en not_active Expired - Lifetime
- 2002-04-18 PT PT05014117T patent/PT1598340E/pt unknown
- 2002-04-18 NZ NZ528977A patent/NZ528977A/en not_active IP Right Cessation
- 2002-04-18 KR KR1020067024967A patent/KR100878774B1/ko not_active Expired - Fee Related
- 2002-04-18 DE DE60231257T patent/DE60231257D1/de not_active Expired - Lifetime
- 2002-04-18 CZ CZ20032850A patent/CZ20032850A3/cs unknown
- 2002-04-18 DK DK05014115.9T patent/DK1598338T5/da active
- 2002-04-18 AT AT05014115T patent/ATE423098T1/de active
- 2002-04-18 HU HU0401109A patent/HUP0401109A3/hu unknown
- 2002-04-18 MX MXPA03009600A patent/MXPA03009600A/es active IP Right Grant
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2003
- 2003-10-17 NO NO20034661A patent/NO20034661L/no not_active Application Discontinuation
- 2003-10-19 IL IL158484A patent/IL158484A/en not_active IP Right Cessation
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2005
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2009
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- 2009-02-23 US US12/390,683 patent/US7939670B2/en not_active Expired - Lifetime
- 2009-04-29 CY CY20091100475T patent/CY1109053T1/el unknown
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- 2009-06-24 JP JP2009150370A patent/JP2009263380A/ja active Pending
- 2009-06-24 JP JP2009150368A patent/JP5081870B2/ja not_active Expired - Fee Related
- 2009-06-24 JP JP2009150369A patent/JP5189562B2/ja not_active Expired - Fee Related
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2010
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2011
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